Queen J of Constance
by literati007
Summary: Jenny Humphrey is the new reigning queen of Constance now that Blair Waldorf has graduated. With Blair gone, she expects an easy year with no cat-fights and no drama. Regardless of Blair's attempts to step in and take charge, Jenny stands her ground. How does this one simple action change the future course of events? Set at the start of season three.
1. Chapter 1

_Starts off from Dan de Fleurette (3x04)_

 **X**

The early morning bell rang. Jenny walked with Eric, her arm draped around his shoulder as the two laughed at a joke he made.

"Eric," Jenny said in a chipper tone, "Constance is gonna be _so_ different. There's no more hierarchy. No more mean girls. No one copying how the queen dresses. It's gonna be a new era of sunlight and fairness."

Eric snorted. "Yeah, I don't think that's what Blair had in mind when she picked you to be her successor," he remarked in amusement.

He was probably right. Thankfully, Jenny couldn't care less what Blair thought. Now that the former headband-wearing-queen-bee was no longer a student at Constance, things would finally be different. For starters, the usual start of school jitters Jenny had felt since freshman year had resided, and in its place, a light and giddy feeling.

"Too bad," she said with a casual shrug. As she stared at her best friend, she suddenly remembered his boyfriend. "Hey, when does Jonathan get back from his fencing camp?"

"Not till next month." Eric shook his head, as if the thought disappointed him.

"Jenny!" an eager voice rang out, cutting their conversation short.

Jenny and Eric both shifted their attention, only to find three girls, adorned in very similar outfits to Jenny's, rushing toward them. Upon closer inspection, their makeup too was reminiscent of Jenny's alternative style.

Though Jenny kept a cool facade, Eric couldn't help but let his jaw drop.

"Oh, that's disturbing."

Once they got closer, the girls smiled at Jenny, waiting for her acknowledgement. The blonde seemed to pick up on this as she quickly addressed them, "Uh - Hi. Who are you?"

The girl in the middle, wearing the red leather jacket, spoke up. Jenny assumed she had the most authority within the group.

"I'm Carmen. This is Celeste," she said, pointing to the girl on her left, wearing a black leather jacket. Celeste gave Jenny a little wave. Carmen then pointed to the girl on her right and said, "That's Jane. We're here to make sure you get _exactly_ what you want this year."

Jenny blinked, unsure if she had heard the girl correctly. A quick glance at her step-brother, who appeared astonished by the proclamation, confirmed her hearing.

"You're gonna rule the school with an iron fist," Celeste said proudly.

"Okay, enough," Jenny said, having heard enough of their nonsense. "First, go wash your eyes, and second, tell everyone I need to talk to them now."

At the sheepish looks, Jenny nodded her head adamantly and said, " _Now_."

With reluctance and sighs, the trio departed. Eric turned to Jenny with a smirk. "So, a new era of sunlight and fairness?"

She rolled her eyes at his unwavering sarcasm. "Shut up," she muttered, to which he only laughed harder.

This was undoubtedly going to be a long day.

* * *

A few moments later found Jenny in the courtyard, stood on top of a table as she addressed the crowd of Constance students in front of her.

"There is no more hierarchy," she declared, encouraged by several nods from the crowd. "The steps of the Met will no longer be restricted to a certain crowd. No more nar-tinis. No more headbands. This is a _new_ era. Let freedom reign."

At the applause of her fellow classmates, Jenny failed to notice one very important detail. Celeste, Carmen and Jane all exchanged suspicious glances before the former dug into her purse and pulled out her phone.

With just a simple text message, all hell was about to break loose.

* * *

"This is _not_ a democracy, ladies. Everyone does not get a voice, and that's okay."

Jenny frowned in confusion at the sight before her. Celeste, Carmen and Jane were stood in front of a crowd, hands on their hips as they berated their fellow classmates, even going as far as to make one girl cry. Suddenly, she knew what was going on. Clenching her fists, Jenny made her way towards them, with Eric by her side.

"What is this?" she demanded angrily. "Did you not hear me this morning?"

Carmen smirked, "Oh, you mean your cute little attempt at perestroika?"

"We're going back to the old way: queens, hierarchy, and no _Brooklyn_ wannabes," Jane added, eyeing Jenny in distaste. "Sorry, Little J."

"Who told you to call me that?" Jenny asked, though she already knew the answer. There was only one person malicious enough to ruin her credibility.

The trio sauntered off, ignoring her completely. Eric sighed, watching them go.

"Okay, unless I'm blind, their headbands were monogrammed with BW," he observed, staring at his best friend in concern.

Jenny huffed. "What a surprise."

As cool as her exterior was, internally she was seeing red. It seemed Blair had yet to loosen her vice-like grip on the school, and was unwilling to let the social hierarchy crumble. The thing that Jenny didn't understand was why that was. Blair had already graduated and was now in college. Surely she'd be too busy to engage in such trivial matters? But then again, this was Blair Waldorf - meddling was her middle name.

Clutching her bag tightly, Jenny scowled. No matter what stunts Blair would pull, she would stand her ground. Constance _would_ become free of the hierarchy. This was a new era.

And Little J from Brooklyn would make sure of that.

* * *

"Congratulations. Your girlfriend has installed a puppet regime," Jenny said, leaning back against Chuck's limousine. The boy in question shook his head with a smirk.

"Blair's gone Colonel Kurtz. She needs to be back to reality," he said a matter-of-factly.

He stuck his hands in his trouser pockets and regarded Jenny carefully, who remained silent. "Help me, and I'll help you take back the crown."

Resisting the urge to scoff at his request, Jenny stared at him incredulously. "Why? They don't want my kind of leadership. They want a tyrant who'll police their behaviour and chart their movement on the social ladder."

The corner of his lips twitched upwards. It was so faint that she thought she imagined it.

"Find someone else."

"I need _you_ ," he insisted, nodding his head in determination. His words were sharp though his inflection was soft. "You're fooling yourself if you don't think you were born to rule this school."

"People change, Chuck," she said, folding her arms across her chest. Not that she expected him to understand, he was always the same self-entitled, rich kid.

"Not you," he replied with a gaze that felt as though he were looking right through her. She shifted uncomfortably. "Not about this. The Jenny Humphrey who used to sit in Brooklyn and watch the lights across the water?"

Jenny shrugged, trying not to show how badly his words affected her. She absently wondered how he knew all of this, but didn't press it.

"Who went toe-to-toe with Blair Waldorf and actually won her respect?" he continued persistently. "You can't tell me that girl isn't still in there. Now that the dream is coming true, you owe it to her to live it."

Closing her eyes, Jenny took a deep breath to steady her nerves. She didn't owe anyone anything. Especially Blair. But with the way Chuck had stared at her, as if he expected so much more from her, she slowly felt her resolve crumble. Maybe it wouldn't hurt to go along with his scheme, after all. Maybe it would work, and Blair would back off. That alone was worth the attempt.

"Blair doesn't want me to be queen," she admitted, opening her eyes to look at the dark-haired-boy beside her.

He didn't waver. "Well, maybe we can make her reconsider."

* * *

Now that her father was about to remarry and Dan was at college, Jenny felt more alone than usual. Thankfully, life had blessed her with a soon to be step-brother who doubled as her best friend, and in times of crisis he was always there for her, much more so than her own kin were.

"Eric," she wailed, laying on his bed with a pout after having recapped her earlier conversation with Chuck. "What am I going to do?"

"Hang on a second," Eric replied, typing away on his computer. His fingers were practically banging the keyboard at lightning speed and his eyes were glued to the screen. Out of curiosity, Jenny sat up on the bed and squinted to see what he was doing.

"Uh - earth to Eric? Are you even listening to me?"

Eric didn't reply, he continued typing until he was done. "There," he said, hitting the send button. "I was just writing an email to Jonathan, updating him about our first day. And don't worry - I _was_ listening, why do you think I took extra long to type everything out? I couldn't miss out a single detail or Jonathan would have killed us both."

"Uh huh," Jenny said, rolling her eyes. "Back on topic - what do you think I should do?"

"Well," Eric said, leaning back in his seat, "as tricky as the situation is, I think the solution is quite clear."

Jenny raised a brow. "You do?"

"Yeah. I think my step-brother - er, _ex-step-brother_ , is right. As annoying as he can be, Chuck means well. His plan is solid and will definitely give Blair a reality check."

"I'm not sure about that," Jenny said, tugging at his bed sheets. "Blair has a jealous streak. What if when she sees Chuck and I together at the premiere, instead of snapping out of whatever haze she's in, she decides to never let me take back the crown."

Eric scratched his head as he considered this. "That is a possibility. But again, I think Chuck would know best. I mean, he _is_ dating her. I'm sure he's thought it all out."

"I suppose that's true." Jenny hoped he was right. She didn't want any more drama than necessary. After the train wreck that was last year, she'd had enough drama for a lifetime.

With determination, she stood up and headed for the door.

"Hey Eric, can you help me pick out what to wear tonight?"

* * *

The limousine door opened and Jenny climbed out. The khaki green dress that Eric had picked out for her fitted like a glove, which she paired with a statement necklace and killer heels. Her hair was let down in an array of soft curls and her makeup bold.

Chuck stared at her, momentarily surprised, before he recovered.

"Exquisite. You exceed even my high expectations," he said smoothly, in that low baritone of his.

Fighting back a blush, Jenny smirked at him, meeting his gaze. "I'm _only_ here for the good of the school, Chuck."

He stared back and said, " _I'm_ only here for Blair."

They continued to stare at one another a moment longer before Jenny walked away with nary a backward glance, unaware his eyes stayed glued onto her retreating figure, a puzzled expression on his face.

* * *

The premiere was actually quite fun. Much more than Jenny had initially expected. The movie was great, Olivia was nice and the food was to die for. So far, Blair had yet to turn up, though after the gossip girl blast she had sent out, that would no longer be the case.

Her thoughts were confirmed when the overly ambitious brunette stormed her way towards her.

"Did you really think your lame attempts to embarrass me…" Blair shouted, uncaring of the little audience she had garnered from her outburst.

Jenny felt uncomfortable with all the watchful eyes and so interjected, "Blair! Stop it."

"...would help you get back queen? I _will_ make your life a living hell."

"Blair!" Jenny tried again.

Chuck chose the perfect moment to cut in. He grabbed Jenny by the shoulders and positioned her away from his girlfriend.

"It wasn't her idea," he said calmly.

Blair was taken aback, her mouth hung open, and Jenny decided that now was a good time to walk away. She didn't want to witness an argument between the couple. They were already psycho enough that it would no doubt escalate into war. With a pointed glance at Chuck, she let her feet carry her away to where her father stood with Lily.

* * *

"So, how did it go?" Eric asked her as soon as she had entered the penthouse.

"As expected," she replied, kicking off her heels before joining him on the couch. "Blair kicked off. Chuck intercepted and I walked away."

Eric leaned forward in interest. Ironically, he held a packet of popcorn that he was munching on as he waited for her to say more.

Jenny sighed. "In other words, the whole thing worked out in Chuck's favour and not _mine_."

"Really?"

"Unfortunately. After tonight, she _definitely_ doesn't want me to be queen. It seems my reign was short-lived, it has to be a record or something."

"Hmm," Eric hummed in thought, "maybe it doesn't have to be."

"What do you mean?" Jenny asked curiously.

"Well, let's say when we get back to school, you continue to play the role of queen," Eric explained, putting down his bag of popcorn. "You know, being bossy and ordering your posse around all day. No one would stop you, not even Blair, because to them, that's the way things should be. No one would expect you to take down the social hierarchy from the inside."

"Take down the social hierarchy from the inside?" Jenny asked, turning the words over in her mind. "That's genius, Eric! Why didn't I think of that before?"

Eric grinned. "Maybe because you don't possess the kind of intellectual superiority as I do?"

Before he knew it, Jenny lobed a pillow right at his face.

* * *

Jenny sat alone at a table in the courtyard. She was soon approached by Carmen, Celeste, and Jane, all of whom were dressed in another attempt of replicating her sense of fashion. Unlike last time, Jenny didn't bat an eyelid.

"Hey, Jenny. Is there anything we can do for you?" Celeste asked.

Jenny regarded them with a cold look. One that she had spent hours perfecting. If she wanted to play the part, she had to look the part.

"Actually," she drawled, "go make sure my spot's free at the Met steps. And wait there with a yogurt for me."

The girls nodded eagerly, pleased that their queen had finally given her first command. As they scurried away, Jenny felt the overwhelming guilt wash over her.

.


	2. Chapter 2

**Chapter Two**

* * *

 _This follows the episode Rufus getting married (3x05). I wanted a chapter where we really see Jenny bond with her family and this episode was a great one. After this chapter, we'll see more of Constance and the story will slowly start diverging from canon._

 **X**

To say things were awkward between Rufus and Lily was an understatement. The tension between the two was so thick that you could cut it with a knife. Jenny and Eric had decided to put their latest plans regarding Constance on the back-burner until the two resolved their issues. It really was dampening everyone's moods.

"Hey, what's going on with Mom and Rufus?" Serena asked, just as Eric and Jenny had entered the room.

Jenny was surprised that the older blonde was clueless about the situation. "Oh, you didn't know? They've been in a cold war since the day you left," she explained.

"Over _Brown_?" Serena asked with a huff. Incredulity was written all over her face.

"On the surface, yeah," Eric said, nodding his head. "But, I have a feeling Mom's flipping out about other things, too."

"They could be in real trouble," Jenny added in concern. Even though she found the whole argument ridiculous, she knew Eric was right. It wasn't simply an argument about Serena, but other things lurking beneath the surface.

"We have to do something about it," she continued. "Dad and Lily really love each other and I don't want them missing out for the second time in their lives all because of one fight."

If there was anyone who deserved love and happiness, it was her father. And she would do anything to help him achieve it, especially after all the hell she had previously put him through. She kind of owed it to him.

"I agree," Serena said, standing up from her chair. "We just have to get them into the same room so they can talk things through."

"And how are we going to do that?" Eric asked. "If one walks into a room, the other walks out."

Serena smiled. It was a smile full of promises and mystery.

"I have the perfect idea. All we need is a restaurant, a reservation and one table. Oh, and call Dan. He'll need to be a part of this."

* * *

Hours later found the Humphrey's at their favourite restaurant. Jenny loved it there, they've been coming to Tony's ever since she was a little girl. It was located in the perfect vicinity between Manhattan and Brooklyn, between both of her worlds.

"This was a great idea, guys," Rufus said, picking up a menu. "I needed some family time. Let's order."

Jenny shot a glance at her brother, who discreetly shook his head. Needing to buy more time before the others arrived, she quickly blurted, "Uh, no. I'm still deciding."

"Jenny, you've been eating the same thing here since you were eleven," Rufus pointed out before eyeing her suspiciously. "What's going on?"

Luckily enough for Jenny, she didn't need to answer for the others had arrived just in time.

"If KC is texting you, you should go," Lily's voice rang out, clear as day.

"I will in a minute," came Serena's reply.

The Humphrey's all glanced up from their menus. Jenny noticed her father watching Lily with a pained expression.

"Well, the three of us can do a family lunch any time. Some other -" Lily trailed off once she caught sight of Rufus.

"You're kidding."

"I _knew_ I let you kids watch the Parent Trap one too many times," Rufus muttered under his breath.

Dan ignored his father's sarcasm and said, "It's time for you to talk."

"You love each other!" Eric insisted to his mother.

"And it's not Rufus' fault that I made the decision not to go Brown," Serena chimed in.

Jenny gave both adults a pleading look and asked, "Can you please sit down? For us?"

It seemed their tag-team efforts had worked. The corners of Lily's mouth turned upwards as she admitted, "Well, I do love the Bolognese here."

As the adults sat down, the children walked away, smiling at each other.

"We make a good team," Eric announced, giving Jenny a high-five which she happily returned.

"Yeah we do. I can't believe that actually worked," Dan said, grinning at his co-conspirators.

Serena smirked, "I know, I'm a genius."

* * *

Things were looking up. Rufus and Lily were getting married that very day and no one could be any happier.

"Oh, Jenny, it's gorgeous," Lily exclaimed, staring at herself in the mirror. She wore a custom made pearly purple dress that her soon to be step-daughter had designed in such short notice.

"Thanks," Jenny replied with a smile, making some final alterations to the dress. When she was done, she took a deep breath and gazed at the woman in front of her.

"You know, Lily, it wasn't easy for me when my parents split up. And, uh, it was even harder when I realised my dad was in love with someone else," she paused, thinking her words carefully. It was so much easier in her head than having to say it out loud.

"But the truth it, I've never seen him happier than he is with you," she finished sincerely. Through the mirror, Lily's eyes met hers as she flashed her a grin.

"That is so sweet," she said, giving Jenny a kiss on the cheek.

"I can't wait for you to hear his vows. They're all about your future together, and … I don't wanna spoil them, but they're really beautiful."

Unaware of the inner turmoil Lily was currently facing, Jenny glanced at the clock. "I'm gonna go. You look amazing. See you out there."

Giddy with excitement, Jenny went to look for her brother and Vanessa. She was really looking forward to having Lily as a stepmother.

* * *

"Hey, Humphrey."

Jenny turned around only to find a certain poofy-haired brunette, in a purple suit, standing in front of her. She folded her arms across her chest and gazed at him warily.

"What do you want, Chuck?"

He gave her one of his weird smiles that wasn't genuine in the slightest. "Nothing," he said in an even tone. "I'm just bored."

She quirked a brow and said, "That's not my problem. Where's your other half? Surely she should be the one to entertain you."

"Blair's currently sniffing around Nate's latest toy, trying to find out any juice that she can report back to him," he said with a roll of his eyes.

"Then why don't you join her?" she pressed.

Chuck straightened his back. "I already know everything I need to," he answered back. He pointed to the bouquet she was holding. "Nice flowers, by the way."

"Thanks," she said, slightly confused by his attitude. She wondered why he was talking to her when there were loads of other people available. For instance, Eric and Dan were standing not too far away, engaged in a casual conversation that he could have easily joined. This was further proven when Georgina Sparks came marching up to Dan, capturing everyone's attention.

"I've been looking everywhere for you," she said, running a hand over Dan's shoulders.

Jenny watched on in confusion as her brother grabbed Georgina by the arms before steering her away. Eric moved closer to where she stood with Chuck, and no sooner were they joined by Serena.

"What is that psycho doing here?" Chuck asked, eyeing the back of Georgina's head in contempt.

"I have no idea, but I'm going to find out," Serena said before striding over to Dan.

* * *

The moment was finally here. The choir played the bride's chorus, the guests were all seated and Jenny stood at the altar with her brother and soon to be step-siblings. Within a few minutes, her father would marry Lily and they would all become the family they were always meant to be.

Things, however, didn't go according to plan. Instead of a bride and groom, there was an awkward pause.

Serena was quick to step forward and smooth things over. "Uh, I'm sorry, everyone. There's been a slight delay. Uh…"

At the sight of Georgina walking towards them, she trailed off.

"...I'm sure there's just a tear in her hem or something. I'll check and I'll be right back," Serena finished, right before following Georgina into the canopy of trees. Jenny, Eric, Dan, Chuck and Blair all followed suit.

* * *

Spotting their parents, the group hurried over towards them. Jenny noticed Scott storm away in the opposite direction. What on earth was going on?

Her question was eventually answered by Georgina of all people, who had exposed Scott as the love child of Lily and Rufus.

"Congratulations, it's a boy," the girl said haughtily before scurrying off.

No one chased after her. Instead, they all stared around, wide-eyed. _It couldn't possibly be true_ , Jenny thought. Surely she would know if she had another brother in such close proximity to her.

But when she glanced over at Dan, she saw the guilt etched across his face, and suddenly she knew that Georgina had been telling the truth.

* * *

"Dan," Jenny said, taking a seat next to her big brother. "Why didn't you tell me about Scott?"

Dan shifted uncomfortably in his seat. With a sigh, he said, "I only just found out yesterday. With the way things were going, I thought it was best to wait until after the wedding."

She nodded, understanding where he was coming from. "It's just so hard for me to wrap my head around. We have _another_ brother."

"I know," Dan said. "It's sad to think we've spent all our lives up until this point not knowing he even existed."

"And all _his_ life he's been searching for his biological family," Jenny pointed out glumly. "I just hope Dad and Lily find him in time."

"Me too."

In a very Dan-like move, he placed a hand on her shoulder and gave it a squeeze.

"At least I have you, Jen."

* * *

Jenny watched with a smile as her father and Lily read their vows in the loft. It really was as beautiful as she had imagined.

Standing next to Dan, the two were engulfed in a bear hug by their father. "I love you guys," he said affectionately.

"We love you too, Dad."

Next, came a hug from Eric.

"We're _finally_ step-siblings!" he exclaimed happily and she laughed harder than she had all week.

The duo decided to look for their half-brother, and found him talking to Dan.

"See, I told you," Jenny said, pointing to Scott, who looked confused. "He has _my_ nose."

"Uh, maybe, but those are _my_ eyebrows," Eric shot back.

Chuckling, Jenny turned back to Scott, who seemed amused by their banter. "So, Scott. What do you think about board games?"

"Love them," he answered without hesitation.

Dan snickered. "Oh, he's _definitely_ one of us."

* * *

The night was filled with festivities, dancing and laughter. Jenny danced with her father, Dan, Eric and even Scott. After talking to her half-brother for a while, she had to admit, he was a pretty cool guy. Too bad he had to return to Boston the following day. But he promised to visit soon and she held onto that. Jenny wanted to get to know him more after missing out for several years.

After tonight, she had felt closer to her family than she had in awhile.

.

* * *

 _To the guest who left a review yesterday, thank you, I really appreciate it! And I agree with everything you said, I really do think Chuck and Blair played a major role in shaping Jenny into who she became. And yes, I cannot wait to write about Jenny and Eric breaking boundaries within the social hierarchy, it's going to be so much fun!_


	3. Chapter 3

**Chapter** **Three**

* * *

 _This chapter loosely follows How To Succeed in Bassness (3x07)_

 **X**

Jenny stood in her room, sorting out the mess that was her bed. There were boxes and boxes of clothes that she had to go through. Thankfully, Lily had offered to assist her.

"Jenny, please let me go through this closet," she practically begged. "There's no room for your new things."

She held up an old dress that Jenny hadn't worn in years and asked, "Does this even fit you anymore?"

"Yes," Jenny answered, taking the dress out of Lily's hands and hanging it back into her wardrobe. " _Perfectly_. All of it does."

Those dresses were all apart of her old life, one that she didn't ever want to forget. Just because she had moved into a penthouse in Manhattan didn't mean that she was going to leave her old life in Brooklyn without looking back. Even if that dress Lily had pointed out no longer fitted her, Jenny wanted to keep it as a reminder of her roots. After all, no matter how hard you tried, you simply couldn't erase your past.

* * *

"So, Rufus asked my size this morning. Does this mean I'm getting a flannel?" Eric joked.

Jenny shot him a grin as they wandered outside the Met. "No. He's just a costume enthusiast. He likes Halloween more than Christmas and his birthday."

"His _own_ birthday?" Eric asked, feigning a gasp.

"I know right! He takes it way too seriously, if you ask me. So, we have to find a party, otherwise I swear he's gonna make us hand out candy dressed as the Octababies."

Eric diverted his attention elsewhere. "Uh, speaking of creepy social anomalies," he said, pointing at Jenny's social-climbing minions. Her eyes followed the direction of his finger and watched as the girls battled over a yogurt pot.

"The last time you handed her the yogurt, there was a spoonful missing," Carmen told Jane in a condescending tone. She snatched the pot out of the meek girl's hands. " _I'll_ give it this time."

"Uh oh, I smell a cat-fight," Eric said, letting out a low whistle. Jenny nudged him in the ribs, amazed by his incessant need for sarcasm.

"This isn't funny," she moaned, "they're insane! How am I going to change _that_?"

"You'll find a way," Eric said, patting her shoulder. "You always do. I'm going to go find Jonathan, now. Your kingdom awaits."

"Ugh, don't leave me."

"You look _queentastic_." He gave her a final pat in reassurance and left.

Mentally bracing herself, Jenny straightened her shoulders and sauntered over to her minions, who upon her arrival dropped all conversation and ran over to her eagerly.

"Your yogurt with almonds," Carmen said, presenting the yogurt pot as if it were some prestige award. "It's all there this time, I checked."

Jenny was about to thank her but stopped herself. Instead, she glared down at the pot as if it had personally offended her and asked, "Are there skin on these almonds?"

She deftly handed it back to the girl and said, "Fix it, and in a timely fashion, otherwise you're all going as the Real Housewives of New Jersey for Halloween."

With a gulp, the girls retreated. Feeling ashamed of herself, Jenny walked up the Met steps, only to find Eric and Jonathan already there.

"Jenny," Jonathan happily called out, "you should come to the Village with us."

"Sure, I'd love to," she said, settling onto the step above them. "What are you guys doing sitting up here?"

The sun shone in Eric's face as he squinted at her. "The birds decided to use our usual place as a restroom."

"Oh, gross."

"You don't mind us being here, do you?" Jonathan asked. "I know about the whole no-one's-supposed-to-sit-above-the-queen rule that's followed religiously."

"No worries," Jenny said, waving her hand dismissively.

"Are you sure?" Eric asked. "What if the girls think us sitting with you is a sign of weakness?"

"I could care less. Honestly, Eric, you're my brother, of course I'd choose _you_. You guys are welcome to sit wherever you want, and technically I _am_ sitting above you. And, since I'm queen, the others would just have to suck it up."

The concern didn't leave Eric's face though Jonathan appeared happy by her decision. When her minions eventually returned with a fresh yogurt pot, they threw sour glances at the boys but other than that, they didn't say anything. If they considered it a sign of weakness, they didn't let it on. Instead, they gushed over Jenny and her latest fashion creation, no doubt trying to secure their positions on the social ladder.

* * *

Chemistry was, in Jenny's opinion, a colossal waste of time. Why did she have to take a class which had nothing to do with her future aspirations? As usual, she zoned out while the teacher lectured the class. She was dragged back to reality, however, when she felt someone jab her arm.

"What?" she snapped at the offender, who in turn gave her a sheepish look.

"Sorry. We're supposed to be lab partners." The girl held out a hand, waiting for Jenny to shake it. Jenny studied the girl carefully, from her pink hair down to the doc martens she was wearing, and found that she admired the girl's style.

"I'm Anna," the pink-haired girl introduced herself as Jenny shook her hand.

"Jenny," she said with a nod.

"I know who you are."

"Alright then. What are we supposed to be doing?" Jenny asked, opening up her textbook. She snuck a peek at the board and turned it to the according page.

"We're meant to be performing the oxidase test," Anna said, scrunching her nose. "Honestly, I was barely paying attention."

Jenny snickered. "Same, and here I was hoping at least one of us did."

"Guess we'll have to improvise," Anna said, removing the stopper from the oxidase solution. She pushed the box of capillary tubes towards Jenny, who picked one up and observed it as if it were a foreign object.

"What am I supposed to do with this?"

"Dip it into the bacteria plate and then dip it into the oxidase solution," Anna instructed, reading from the textbook.

Jenny complied and watched as the solution started bubbling.

"Whoa, that's awesome!" she said, amazed. "Anna, you should really have a go at this, it's so fun!"

She glanced up and noticed Anna watching her studiously. Once the girl realised Jenny had caught her, she quickly shook her head and focused back onto the experiment. Jenny frowned, wondering what that was about.

Working at a fast pace, the duo finished ten minutes earlier than expected. Since they had nothing to do before the bell rang, Jenny decided to get to know the girl. After all, she would be her lab partner for the remainder of the year.

"I really like your hairstyle," Jenny complimented. "I would never be brave enough to go for a shocking pink."

"Thanks," Anna said, running her hand through a couple strands. She seemed hesitant, as if she couldn't believe she was actually talking to Jenny. "I was initially going to go as a redhead, but I'm glad I settled for pink."

"It really suits you."

Anna smiled. "You know, you're different than how I expected you'd be."

"Oh?" Jenny quirked a brow. "How so?"

"Not so stuck up," Anna said, shrugging her shoulders. "I heard rumors that you had a stick up your ass, but you seem quite down to earth to me."

Jenny blinked, unsure if she should take that as a compliment or not.

"Um, thanks?"

"Sorry, I didn't mean that in a rude way! I apologise if it came across like that," Anna babbled. "What I meant is that as queen, I expected you to be more like what's-her-face from last year. Now _she_ was a real piece of work. But you're much nicer."

Now _that_ was a compliment. Laughter escaped Jenny's mouth, and just like that, she had made a new friend.

* * *

"I'm telling you, Eric. They're driving me crazy. I cannot wait for this all to be over," Jenny said, adding the finishing touches to her costume.

"Tell me about it," Eric muttered. "Since Jonathan and I sat with you this morning, they've been glaring at me since. I think they wanna crucify us or something."

Looking in the mirror, Jenny sighed. It felt as though something was missing from her outfit, but she couldn't think of what.

"Here." Eric handed her a black fedora. She put it on, and the effect was instant. Her costume no longer looked like a prison jumpsuit but now a chic 1920's gangster. She absolutely loved it.

"At least we're free from them tonight," she assured him. Although she was allowed to invite anyone she wanted, she wasn't stupid enough to go through with it. If she had, she'd be stuck on queen duty all night and would miss out on all the fun. Besides, she needed some quality time with Eric and Jonathan, especially since she barely hung out with them at school.

In the living room, Jenny spotted her father dressed as one of the Ramones. He was holding a bucket of candy and was grinning from ear-to-ear in excitement. Jenny suspected he might have had some candy himself and was currently experiencing a sugar rush.

"I still think you would make a great Joey," he told her. "The gangster costume is so _1920's_."

"Ha-ha," she deadpanned. "How much sugar have you had?"

Rufus grinned, "I don't know what you're talking about."

"Nice try, Dad. We both know about the intense sugar rush you get every Halloween." She scanned the room for her stepmother. "Lily!"

* * *

The party was in full swing by the time they arrived. The band played some fiery tunes, bubbles were in the air and the flappers danced like there was no tomorrow. The atmosphere was absolutely buzzing with life. Chuck had done an amazing job, it really did feel like a speakeasy.

Jenny walked around looking for someone to talk to since Eric and Jonathan were otherwise preoccupied. With no one around, she picked up a champagne flute and took a sip.

"Isn't it past your bedtime?" asked the familiar baritone voice.

Jenny froze mid-sip, but was quick to regain her composure. "Nope," she said, glaring at the boy. "Don't have one."

Her answer seemed to have amused him, the corners of his lips twitched upwards. "Either way, you really shouldn't be drinking."

"Oh, come on, Chuck. We both know you were practically the poster child for underage drinking," she said with a roll of her eyes. "Besides, it's a _speakeasy_. What's the point, otherwise?"

"Fair enough," he said before checking his wristwatch. "Enjoy the party, although it won't last much longer."

Frowning, she didn't even have time to decipher what he had meant. As soon as Chuck left, he was soon replaced by Nate, who asked her if she wanted to dance. With a grin, she agreed.

"It's been a while, Jenny," he said, twirling her around. She giggled as she fell back onto him. Nate was fun to be around, she always had a good time. Ever since her silly crush on him last year, Jenny had swiftly moved on and found that they were better off as friends. No longer was she so tense around him and was now able to enjoy herself.

"Well, things have been hectic lately, with you in college and me as queen."

Nate chuckled as he spun her around the dance floor. "And how's your queen duties going?"

"Terrible," she admitted. "It's hard following Blair's legacy when it's not the kind I want."

"Bummer. But you and I both know that you'd make a great queen with the way you _want_ to rule. Just follow your instinct and don't try to live up to other people's expectations." At the last part, Jenny knew he was referring to his own experiences. In the past, Nate had continually tried to maintain the image as the golden boy. Up until it burnt him out, that is.

"Thanks, Nate. I'll keep that in mind."

* * *

"Hey, kids. How was the party?" Lily asked as they entered the penthouse. Jenny and Eric exchanged amused glances.

"It was fun," Jenny started.

"Up until it got busted," Eric finished.

Lily's eyes widened before she scrambled for her phone. "Oh, Charles," she muttered, dialling his number. Jenny was so glad she wasn't in his shoes right now, he was about to receive the lecture of a lifetime.

Back in her room, Jenny stared at her reflection once more. Taking off her costume pearls and fedora, she smiled. She may be living in Manhattan, but she was still the girl from Brooklyn.

.


	4. Chapter 4

**Chapter Four**

* * *

 _Ta-da, an original chapter! This was in fact inspired by Blair's annual Waldorf Sleepover_

 **X**

"Are you sure you wanna do this?" Eric asked, glancing down at the finely laminated card in his hand. It wasn't just any card - it was an invitation, one that he had been working on all day to perfect.

With a careful finger, Jenny traced the beautiful calligraphy her step-brother had taken the time to craft for her. _Humphrey Sleepover_ , it read, a mirror image of Blair's annual 'Waldorf Sleepover', but with a twist. Instead if nair-tinis and mani-pedis, there would be board games and hot chocolate.

"Positive," she said with conviction. "It's the perfect way to bond with the girls and hopefully get them to change their mindset."

Eric neatly trimmed the edges of each invitation before enclosing them into little black and white envelopes. "I'm with you about the bonding part, but I'm not entirely sold on the changing their mindset part. I mean, do you know how stubborn these girls can be?"

Jenny scoffed, chucking a paper ball at him, which he narrowly missed. "Um - as a girl, I take offence."

"Well, you _can_ be stubborn at times," Eric admitted, without missing a beat, "but at least you're aware that there's more than one side to a story. Other girls are so caught up in their ways to even consider another point of view."

A brief image of Blair flashed across her mind. Then Serena. Then all the other upper east side girls who Jenny went to school with. They all were exactly the type of girls Eric was referring to. From their insistence that the world revolved around them down to their failure to see the bigger picture, and how their actions could affect others. At one point in her _own_ life, Jenny had been guilty of doing the exact same thing. It was fairly easy to lose yourself in the upper east side. In a crowd full of rich kids, she had felt like a lamb amongst the lions, someone who was an easy target, and in a desperate attempt to prove herself, to show that she _was_ worthy of their approval, she had lost herself along the way.

It had cost her relationship with her father and brother, her fashion career with Eleanor Waldorf and her brief period of homelessness to show her that. She still remembered the sheer panic she had felt, accompanied by the shame and disgust of her own actions. She really had hit rock bottom, and never did she want to feel that way again.

Perhaps that's why she was so adamant about destroying the social hierarchy - she felt as though it was a contributing factor toward her downward spiral. Jenny hated the entire monarch system. The way the queen had the utmost authority and power to invalidate others was dangerous - not only to her subjects, but to the queen herself. She had the power to destroy the self-esteem of young girls, the same way her own self-esteem had been destroyed, and the ability to corrupt lives at her fingertips. She recalled Blair's harsh reign, the way the older brunette had relentlessly preyed upon the weak and used the elite as her pawns, and much like her predecessor, Jenny was vulnerable to giving into that kind of power. It was enticing and addictive and gave her a certain thrill, but she knew better than to indulge in it. What if one day she had given in and lost herself again? The road to hell was paved with good intentions, but it was one Jenny couldn't risk.

"Ain't that the truth," she said finally. "But it's worth the attempt. Who knows, maybe one of them will give in. It's better than nothing, right?"

"I guess so."

Finishing the last of the invitations, Eric stacked them up into a neat pile on the coffee table. "There," he said, "they should be ready to hand out tomorrow."

"Thanks," Jenny said, grinning. Although this was a mission of sorts, she was still excited at the prospect of hosting a sleepover. The only other sleepover she had been to was Blair's in freshman year, and it wasn't exactly the most fun experience, which was why Jenny was determined to do things her way this time around.

Just then, the elevator dinged and Serena stepped out. She was clutching a large, bulky shopping bag. Hauling it onto a nearby sofa, she smiled and sat down opposite the duo.

"What's all this?" the older blonde asked, picking up one of Jenny's invitations.

"It's for a sleepover Jenny's hosting Friday night," Eric answered.

Serena rose a perfectly arched brow as she studied the invitation. Her expression was unreadable and Jenny wondered what was going through her head.

Eventually, Serena asked, "Like the one Blair throws every year?"

"Sort of," Jenny replied carefully. "Since I'm the new queen, I thought it would be nice to get to know the girls. But I don't want it to be an exact copy of Blair's sleepovers."

"Well, I think it's an awesome idea," Serena said. She put the card back onto the pile and sat up straight in her seat. "Look, Jenny, I need a favor. I know it's short notice, but I really need you to make a dress for one of my clients, or KC will have my head in."

"Oh, uh, what kind of dress?" Jenny asked.

Serena retrieved her shopping bag, containing what Jenny now noticed were a bunch of clothing material, and produced a sketchpad. She flipped through the pages until it landed on what appeared to be a roughly drawn ballroom gown. Jenny tried not to squirm at how badly drawn it was.

"My client is adamant that she wears this particular design," Serena said, visibly cringing at the sketch, "and no other designer is willing to make it."

Jenny could certainly see why, the contrasting red and green clashed horrendously. It was the kind of dress that one _might_ wear in christmas, but it was only October, so the only logical answer was that Serena's client must have suffered from some sort of color blindness. That, and a poor taste in fashion - the dress was all kinds of frilly and looked as if it belonged in the nineteenth century.

"Uh…" Jenny was ready to turn down the offer, but at Serena's pleading pout, she paused.

"Is your client okay in the head?" Eric asked incredulously, squinting at the design as if it were magically going to improve.

"Debatable," Serena said to her little brother, before quickly fixing Jenny another pleading look. "Please, Jenny, do it for me? I'll even pay you!"

She knew Serena wouldn't stop asking until she relented, so with a sigh, she agreed. "Okay, but if she does end up wearing it, can you please not disclose my name to the press? I don't want my name associated with _that_."

"Done," Serena agreed quickly. She got up and engulfed Jenny into a hug. "Thank you so much! You're honestly such a lifesaver."

"Don't mention it," Jenny said. She scanned the contents of the shopping bag. The material was of fine quality, she could work with that. "When do you want this by?"

"Friday night. Chuck and Nate are hosting a party for his cousin Tripp's election campaign at the Empire. So some of my clients are going to be there, Patrick included."

Jenny's eyes widened. That only gave her four days. "Friday?" she exclaimed. "But I have my sleepover to arrange. I'm not sure I can manage all that."

"Eric and I can help with that," Serena said, shooting her brother a pointed look.

"Speak for yourself, I'm not exactly knowledgeable about girly sleepovers," he shot back.

At the panicked expression on Jenny's face, Serena was quick to assure her, "Don't worry, J. I'll handle it. While you work on the dress, I'll arrange everything you need to ensure it's the best slumber party yet."

"Okay." Jenny exhaled noisily.

If she could trust anyone to make arrangements for her sleepover, it was Serena. The older girl had a knack for party planning, seeing as she was an avid party-goer herself.

"I'll get to work as soon as I can," she promised.

* * *

The remainder of the days flew by. As soon as school would let out, Jenny would run home and sit at her sewing machine, spending hours upon hours working on the dress. Sometimes she would miss dinner, but thankfully someone always brought food up to her room. If she wasn't in a frantic rush, Jenny would take a break and eat her meal, but when she was too preoccupied, her food would remain untouched and grow cold.

As she worked on the dress, her mind would often wander back to her sleepover. She had already handed out the invitations to the girls at school, and they had all agreed to come, some even sent her RSVP cards of their own. Jenny hoped Serena had managed to make the suitable arrangements she needed, such as ordering food from her favorite restaurant, Tony's, or ensuring there was enough hot chocolate and marshmallows to go around. Maybe she could even rent some movies that they could watch, like the Notebook. You could never go wrong with a good chick-flick.

Thursday night rolled around and Jenny was finally done. She held up the dress and inspected it carefully, looking for any loose stitches or frays. After double checking and ensuring everything was fine, she called Serena who agreed to come and pick it up.

Eventually, Serena arrived and brought Eric with her, who stared at the dress in undisguised fascination.

"Wow, that's _hideous_ , and I mean that in the best way possible," he remarked, while Serena hummed in agreement.

"I think this is exactly what my client was going for," she said. "Though I have no idea what possessed her."

Jenny folded the dress carefully and handed it to Serena. "Honestly, it's probably the most challenging piece of clothing I've created. I can't say I did a bad job with what I had to work with."

"You did a great job, J. My client is going to love it and KC is going to hate it. Tomorrow is definitely going to be an interesting night."

"Speaking of an interesting night," Eric interjected, "I heard that you'll be spending it with Patrick."

Jenny noticed Serena's cheeks flush as she avoided their gaze. "I won't be spending the night with him. It's just a publicity stunt. I have to pretend to be his girlfriend until he's casted in his next movie."

"Uh huh," Eric continued. "Then why does Blair think you're _really_ dating him?"

"Because she's Blair. What else can I say?"

Serena made her way to the door and Eric followed closely behind. The siblings continued bickering as they left Jenny's room, the sounds of their chatter fading away until nothing but silence reigned. Too exhausted to do much else, Jenny laid on her bed, closed her eyes and fell into a deep slumber.

* * *

Eric and her parents were at the loft, playing board games with Dan and Olivia, which meant that Jenny had the penthouse to herself. The girls would be arriving shortly and Serena had assured her that she had already taken care of the preparations. But when Jenny checked the pantry for all the food she had requested, it was empty.

Grabbing her phone, she quickly dialled Serena's number, but it went straight to voicemail.

"Ugh," Jenny groaned, snapping her phone shut. It seemed her older step-sister had flaked on her, after all. The girls would arrive within half an hour, what was she going to do?

She kicked the couch. "Damn it."

As if luck were on her side, the elevator suddenly dinged and before she knew it, an army of caterers stepped out, pushing carts and carts of food.

"Jenny Humphrey?" one of them asked.

"Um, that's me."

"We've been instructed to serve the food at nine p.m sharp, on Miss Van Der Woodsen's orders. We'll go and set up now."

Though slightly confused, Jenny nodded and watched as the team of caterers wheeled their carts into the kitchen area. She could smell the delicious aroma of roast chicken, stuffed peppers and many more delectables. Okay, so maybe Serena didn't forget about her sleepover, after all. Jenny made a mental note to call and thank her later.

Darting her eyes around the living room, Jenny focused on the trundle beds laid scattered about, adorned with perfectly fluffed pillows and fresh blankets. Each pillow contained an eye mask inscribed with the word _Humphrey_ on it. Initially, she had wanted to go with sleeping bags but stopped short, remembering the crowd of girls she had invited. This _wasn't_ Brooklyn. Girls in the upper east side simply didn't sleep inside sleeping bags, and would rather die than be caught in one.

"Excuse me, did you bring the hot chocolate?" Jenny asked the main caterer. The man squinted down at her in confusion.

"Hot chocolate?" he asked. "I was told we were to distribute gin martinis." He pointed to a cart, containing martini glasses and a bowl of olives.

"Oh, right," she said, masking her confusion. "That's, um, perfect, thank you."

This was starting to feel more and more like Blair's sleepover from freshman year, from the trundle beds down to the gin martinis. She wanted it to be different, distinct, but Serena seemed to have other ideas judging by the way she had organised everything. Jenny took a deep breath to soothe her nerves. Maybe it wouldn't be so bad. The guests had yet to arrive and the night was still young. Who knew how things would turn out, maybe the night would end up surprising her.

* * *

"I really like what you've done with the place," Celeste said upon entering the penthouse. She was dressed in pearls and silk pyjamas. Next to her, Jenny felt inadequate in her night dress.

"Thanks."

Celeste set her bag down on the coffee table and settled into one of the sofas, while the other minions followed suit. Jenny decided now was a good time to give the opening speech.

She grabbed a gin martini and took a sip. "Thank you for coming, ladies. Today is the first ever _Humphrey sleepover_. Only those of you who are worthy have been selected to come, for obvious reasons, and it will definitely be a night to remember."

Raising her glass in the air as a salute, the girls mimicked her gesture before they all took a sip.

"Now, who wants to play a game?"

* * *

Throughout the night, Jenny had noticed Carmen's look of scepticism and wanted to wipe it right off her smug face. Perhaps it wasn't the best idea to start off the night playing twenty-one truths. It wasn't as risque as Blair's truth or dare.

"Alright, ladies," Jenny drawled, "shall we play _Never Have I Ever?_ "

"I don't know, seems a bit _childish_ to me," Carmen replied, folding her arms against her chest.

Jenny shot her a smirk. "Oh? But what if we raise the stakes higher."

This intrigued the other girls. Jane leaned forward and asked, "What do you mean?"

Feigning boredom, Jenny examined her nails and said, "Well, instead of skipping a drink if you've never done something, why not spill a secret. And it has to be a juicy, one that _no one_ knows about."

The minions agreed instantly but Jenny was focused on Carmen, who had yet to answer. Staring her down, Carmen finally flinched at the intensity of Jenny's gaze.

"Fine," she said begrudgingly, propping a pillow onto her lap. "Should be easy."

The corners of Jenny's lips slowly lifted upwards. _Challenge accepted_ , she thought.

"As queen, I'll start," she announced, deciding to start off with something tame. "Never have I ever kissed a boy."

Predictably, everyone present took a sip of their martinis.

"Good. Natasha, your turn."

"Never have I ever made it to third base," the brunette said, to which everyone but Jenny drank.

Instead of feeling ashamed at the pitying glances thrown her way, Jenny decided to manipulate the situation by revealing a secret that would blow them away.

"Last year I may have stolen a jacket from Eleanor Waldorf's boutique, gotten caught and lied to the police. In the end, I managed to trick them into letting me go scott free," she said, taking a sip of her martini regardless.

Celeste gasped and asked, "How did you do that?"

"Oh, you see, I already had a set of keys to Eleanor's store," she said, bending the truth slightly. "I've worked with her before. She called me _extremely talented_. Even told me that I had a career in fashion that would drag others out of business."

"Wow!"

"That's amazing!"

Jenny leaned back in her seat with a grin. Turns out manipulation isn't as hard as she thought. If she kept this up, the girls would definitely respect her as queen and never doubt her authority again.

* * *

The rest of the night flew by. Serena had arranged for massages, manicures and facials, all without telling Jenny, so it came as a surprise to the blonde when the team had turned up. Not that she was complaining, the girls absolutely loved it. As for their games, Jenny had learned a couple of dirty secrets from the girls that she _could_ use in the future, but probably wouldn't. She was long past the days of blackmail and extortion, and didn't want to fall back into that particular rabbit hole. It was a dark and lonely place.

Once the girls were all asleep on their trundle beds, Jenny hastily went to her room, intending to call Eric and update him with their progress. With three rings, he picked up.

"Hey, how's it going?" he asked.

Jenny sighed. "It was a complete bust. I didn't make much progress. Don't get me wrong, we did bond and I think they respect me a bit more than they did before, but ultimately they're still the same shallow, self-entitled girls they were before."

"Well, what did you expect?" Eric said with a scoff. "You can't just change their entire ideologies within a night. If things worked like that, life would be much simpler."

"No need to sass me, mister. I get the message loud and clear. I guess it's back to the drawing board."

"Hey, on the bright side, at least you wasn't stuck with Dan and Olivia, and Mom and Rufus," he complained. "I felt like the ultimate fifth wheel. Your night was certainly more eventful that mine."

Resisting the urge to laugh, Jenny settled for a silent smile. Even without trying, Eric knew just how to make her feel better.

.

* * *

 _thoughts?_


	5. Chapter 5

**Chapter Five**

* * *

 _Based off They Shoot Humphreys, Don't They (3x09) with many original scenes and alterations_

 **X**

Walking down the streets of Manhattan was always an adventure for Jenny. Especially in the mornings. The hustle and bustle of the city while manic certainly kept things alive. It was almost magical, in the sense that the city never slept. It was constantly moving.

The October air was unusually chilly as she huddled closer to her father, thankful for his warm body heat. They were meeting Dan for breakfast in a fancy new diner that had just opened. It was long overdue for a Humphrey family breakfast. Ever since Dan had started NYU, they hadn't seen much of him as he was often too busy, so it was a perfect opportunity to catch up and try new food.

"So, a cotillion, huh?" Rufus asked, tucking his hands into his coat pocket as they headed down the street. She recognised the gesture as one he often did whenever he was embarrassed to talk about something he considered quite girly. A vivid image of the talk flashed in her mind - when she was around twelve and her mother had left, Jenny had started her period for the first time and with no one else to turn to but her father, it had made for a very uncomfortable discussion between the pair.

Jenny smiled fondly as she shook away the memory. "Uh - yeah. All the other girls at Constance are taking part, so it should be fun."

"Right." Rufus nodded, though the concern was visible on his face. Jenny could tell that he wasn't a fan of the idea, but wasn't likely to voice his opinion aloud. If there was one thing she loved about her father, it was his constant showal of support for his children, even if he didn't necessarily agree with their decisions (the only exception being if he thought they went too far - like Jenny often did last year).

"So, um, who's your date?" he asked, scratching the back of his head awkwardly as they entered the diner. Jenny spotted her brother who sat alone, at the far left table near the window, waving them over.

" _Escort_ ," she corrected as they edged closer to Dan, "and I don't have one yet."

As they took their seats, Dan leaned forward in interest and asked, "Who doesn't have what yet?"

"Your sister needs an escort for the cotillion Lily's hosting," Rufus answered, picking up a menu and focusing his attention onto the breakfast items.

"Cotillion?" Dan repeated. "I didn't know you were going to take part in that, Jen."

"I wasn't planning too," Jenny admitted, lowering her voice so that only her brother would hear her, "but as queen of Constance, I _need_ to take part, otherwise it's considered as a sign of weakness."

Dan rolled his eyes the same way he always did whenever Constance was mentioned. He claimed it reminded him of his time at St. Jude's and all the surrounding drama, which he didn't miss in the slightest. "Well, we both know you never back down from a challenge. Why don't you take Eric? I'm sure he's an expert when it comes to these kinds of things."

"I wish. But apparently, since we're now related, he's exempt from having to escort me."

Dan wore a frown. "What a bummer."

"You know," Rufus said, placing his menu back onto the table, "that you don't have to go through with the cotillion if you don't want to. Just because you want the other girls to respect you doesn't mean you have to follow their expectations." It was clear that despite their soft murmuring, Rufus had still managed to pick up on his children's discussion.

"It doesn't work like that, Dad. This isn't Brooklyn - it's the Upper East Side. If you miss out an event like this, you become an instant social pariah," Jenny said with a sigh. No matter how many times she had explained it to him, he never seemed to understand. Much like Dan, her father would fail to see past the superficial layer of glam, couture and quadrilles, and into the bigger picture. She supposed it was a guy thing, they were never much for gossip, and was probably why she found it easier to talk to Lily about certain situations than her own father.

"Well, I'll love you no matter what your social standing is," he said, giving her an affectionate pat on the head.

She batted his hand away and smoothed down her bleached blonde hair. "Thanks, Dad, but I'm pretty sure that it's an unwritten rule to love your child no matter what."

"She got you there." Dan chuckled at his father.

Rufus muttered something under his breath before standing up. Though she didn't catch every word, Jenny was sure she heard him mention something about raising know-it-alls and had to refrain herself from giggling.

"I'll go order. I know you both well enough to know what you want to eat," he said, collecting the menus from the table and striding over to the counter.

As he left, Jenny took the opportunity to stare at her brother, analysing him with both interest and scepticism. He was in an unusually good mood since they had entered the diner and she wondered why that was. Dan was reading something off his phone, a really cheesy grin plastered on his face, and suddenly she realised what the cause of his euphoria was.

Propping both her elbows up on the table and resting her chin on her hands, she gazed up at him with a knowing look. "I take it things with Olivia are going well?" she asked.

"More than well, it's going _amazing_ ," he said, still grinning. "I think I've finally found my dream girl."

Resisting the urge to sigh, she instead flashed him a patient smile. In Jenny's opinion, Dan _always_ thought he found his dream girl - no matter who he was dating, they had always seemed perfect to him until the honeymoon phase finally wore off and the facade faded. Take Serena, for instance. When they had first dated, Dan would often mention how he had lucked out with a girl like her, perfect in every way, shape and form, that was until she was thrust back into the spotlight and the glare of which had almost blinded him. It was a very messy break up, and since then he had sworn off dating celebrities. But then Olivia came along and the rest was history (though in her opinion, she didn't think that would last long, either).

As much as Jenny loved her brother, even she had to admit that his taste in woman was questionable at best.

She opened her mouth to change the subject but was stopped short at the arrival of two unwanted guests. Even the grin on Dan's face faltered by their presence.

"Humphrey. Little Humphrey," Blair Waldorf greeted in her typical offhand manner. Next to her, Chuck gave them a single nod of acknowledgement.

Jenny spotted her father still at the counter, in what appeared to be a deep conversation with the owner of the establishment. She quickly turned to Dan, the two exchanging knowing looks before he finally spoke up.

"Blair. Chuck. What a _pleasure_. Is there anything we can do for the two of you?" he asked, his words coated with a glaring layer of sarcasm.

Blair seemed to have picked up on his tone and smirked. Behind her, Chuck appeared bored as he scrolled through his phone. "Nothing from _you_ , Humphrey. I came over here to speak to Little J, actually. I heard she'll be taking part in the cotillion this year and wanted to wish her luck."

Jenny quirked a brow, wondering what exactly the brunette had wanted from her. "I'm right here," she drawled, "no need to talk about me in third person. And yes, I am taking part in the cotillion this year."

"Well, that's a given," Blair said haughtily. "Every queen takes part."

"Can you make this fast, Blair?" Chuck interjected impatiently, "I have a meeting to attend."

His girlfriend ignored him, placing her hands on her hips as she continued, "Word on the street is that you're still looking for an escort."

"So what if I am?" Jenny huffed, irritated by her incessant theatrics. Blair always liked to make a spectacle of others and wherever she went, she attracted an audience. Today was no exception, the other patrons of the diner were staring in their direction, Rufus included.

"Blair." Chuck sighed, placing an arm on his girlfriend's shoulder, but she shrugged it off.

"Nothing, except it makes the queen look _weak_ ," Blair continued in an even tone. "And we can't have that, now can we, Little J?"

"Look, Blair. Just lay off her, okay? We're here to eat breakfast and mind our own business. Take your theatrics someplace else," Dan cut in, folding his arms as he glared at the couple.

Though she was grateful that Dan was defending her, Jenny wanted him to back off. She hated appearing weak and needing her big brother's help, especially against Blair. She may have loathed the older girl, but somewhere deep down, she still yearned for her respect.

"What do you have in mind?" Jenny asked, meeting her eyes carefully. She could have sworn she saw Blair's eyes soften a smidge before they went hard again. But then again, it was so fast that she may have imagined it.

"Well," Blair began, "we can discuss it at the gathering Lily's hosting tonight. I have plenty of ideas to go about, and as _your mentor_ , I can assure you that this will be a cotillion you'll never forget."

* * *

With a scowl, Jenny peered down at her phone as she read the incriminating blast Gossip Girl had just sent out: _Gossip Girl here. Just like the mob, New York prep schools have their own five families. You may be the John Gotti of Constance, Little J, but that doesn't mean you'll ever be part of this Costra Nostra._

She clenched her fists. Oh, when she got her hands on whoever wrote this -

"Oh, my God! Everyone's here. Come on, let's go and say hi," Sawyer exclaimed, snapping Jenny out of her musings as she and the other minions rushed to go greet the other queens.

Taking a deep breath to soothe her aching nerves, she was quick to slip on a mask of indifference as she watched the scene unfold right in front of her. Each queen glared at her with vehemence, as if she were the gum on the bottom of their cherished Louboutins, and Jenny tried frightfully hard not to squirm under their heavy gazes. Suddenly, she came to an epiphany - she was in way over her head. Being the queen of Constance was one thing, but to compete with the queens of _other_ prep schools was a whole other territory that she wasn't familiar with in the slightest.

She hated to admit it, but maybe she needed Blair's help, after all.

* * *

Clad in an gray wrap dress, Blair looked the definition of poise and elegance. It was almost effortless for her. Jenny watched the brunette carefully as she gazed around the room, her eyes scanned over the other participants in a calculating manner.

A waiter approached them, offering a selection of canopies but was immediately dismissed by a bark from Blair. The former queen bee then turned to Jenny and said, "I'm glad you came to your senses."

Jenny rolled her eyes and was about to answer but was interrupted by her step-sister.

"Blair," Serena said coldly. "There's a list of debs and their mentors on the coffee table. You're more than welcome to have a look at who you've been assigned to. My debs right here, right Jenny," she added, wrapping an arm around Jenny's shoulder.

"Uh…" Jenny trailed off, blinking in confusion. She could have sworn Blair was her mentor as the older girl had told her earlier, but then again she had yet to check the list. Maybe Blair had lied.

"No she's not," Blair protested, "she's _my_ mentee. I specifically put in a request with Lily and she assured me that I'd get Jenny."

"Not according to the list you didn't."

"The list be damned!"

Serena sighed and asked, "Blair, are we really doing this right now?"

"I gave you a chance to apologise," Blair responded, folding her arms across her chest.

 _Ah_ , Jenny thought, _now it all made sense_. Blair and Serena were clearly in another cold war and wanted to drag her into the middle of it. No wonder Blair had been extra eager to take her on as a mentee, even feigning concern for Jenny's escort problem, but of course the older brunette had an ulterior motive. After all, no one acted out of kindness or sincerity in the Upper East Side, a lesson she really should have learned by now.

"How about _you_ apologise?" Serena continued.

Blair scoffed in indignation and said, "I'm here, aren't I?"

Having finally heard enough of their dramatics, Jenny cut in with an impatient remark, "Okay, look. I have enough of my own problems, so I'm not gonna let you guys make me a pawn in your war."

"War? What?" Blair had the gall to look sheepish at the suggestion. "Of course not."

Serena, however, rolled her eyes and grabbed her purse. "You know what, Blair, you can have her. I've got better things to do, like help Congressman Tripp Vanderbilt with his work. Unlike you, I don't need this. These are the last people in New York who still think you matter."

Blair's face fell for a second, as if Serena had slapped her senseless, but was quick to throw back on her mask of indifference. "Well, then go. Jenny's better off with me, anyway!"

Ignoring her, Serena gave Jenny a smile. "Good luck, J. You got this," she said before finally exiting the penthouse.

Muttering a quick ' _thanks_ ', Jenny turned back to Blair, who studied her closely. After a while of uncomfortable scrutiny, Blair grabbed Jenny's hand and yanked her further into the room, no doubt to instill some 'helpful tips' into her young and naive mind. Along the way, she grabbed some champagne. A night with Blair was guaranteed to be a long one.

* * *

"First things first, Little J. We'll need to sort out your escort dilemma," Blair said, pacing around the empty corner of the room she had dragged them into.

Eric, who had joined them not too long ago, added his input, "I can scroll through Facebook, if you'd like? There's plenty of young, hot guys on there."

"It's a start," Blair said in approval. "Good thinking, E."

Jenny sighed. "I just don't get why I can't go with Jonathan," she asked. "I mean, I know he's Eric's boyfriend and all, but he'd still make a great escort. Not to mention I'd have so much fun with him."

"She's got a point. He is a Whitney," Eric agreed.

"Ew." Blair frowned as if the idea was too much for her to stomach. "Definitely a massive no-no. Going with your step-brother's boyfriend? That's entirely out of the question." She continued pacing in deep thought, her hands glued to her hips.

"It's better than no escort right?"

She must have said the wrong thing for Blair's frown turned deeper in disgust. She inched closer to Jenny until they were almost nose-to-nose. Jenny tried not to show how intimidated she was feeling that very moment as she swallowed hard.

"Jenny, when you descend those stairs tomorrow night, everyone there will judge you based on that moment for the rest of your life," Blair said harshly. "This is _not_ like your wedding day. Cotillion only happens once. Now, you already have a strike against you because of the whole _Brooklyn misfortune_. Don't let them pile up."

Pinching the bridge of her nose to refrain herself, Jenny let Blair's dig about Brooklyn slide. Now was not the time nor place to start an argument, especially in front of the other debs. "Okay, point taken," she said, exhaling loudly. "But I don't know who I could possibly find in such short notice."

"Perhaps I can help with that," came a nasally voice. Jenny, Blair and Eric had all turned to the direction of which it came from only to find a short, frumpy-looking girl standing there timidly.

"And who are you?" Blair asked in her typical inquisitive tone.

The girl fidgeted with her dress before she spoke up," Hi. I'm Kira. I go to Constance with you," she said, staring directly at Jenny.

She did look vaguely familiar now that Jenny considered it. "Yeah, sure. I've seen you around."

"You have? That's awesome," Kira gushed, almost star-struck, and Jenny already felt the second-hand embarrassment emanating.

Growing impatient with the small talk, Blair cut in. "That's great and all, really, but _how_ can you help us?" she asked Kira.

Kira smiled shyly and said, "Well, Jenny could go with Graham Collins of course!"

"Graham Collins?" Jenny repeated incredulously, " As in _the_ Graham Collins?"

From beside her, she heard Blair ask Eric who Graham was to which he answered, "Only like the hottest guy on the Upper East Side. He's sort of like our version of Nate."

"Yeah," Kira said eagerly. "Graham lives in my building. We've been neighbours forever. I can ask him for you, if you want."

"I know Graham, too," Eric admitted. "We went to Camp Suisse together. I totally forgot about him, Jen, otherwise I would have suggested him, too."

Trying not to squeal from excitement, Jenny played it cool with a nod. "That's totally fine. I don't mind going with Graham. If you could just send me his number, Kira, I'll text him myself."

"Great. Now that it's all settled, I'll take my leave," Blair said, with her usual resting-Blair face. She leaned in for a hug and muttered lowly so that only Jenny could hear her, "Word of advice, Little J. Get through the night, and the crown remains yours. If you mess up, I'll replace you with someone I see fit."

"Oh, don't worry, I _won't_ ," Jenny said, with newfound determination, hugging the brunette back. If there was one thing she never did, it was backing down from a challenge.

* * *

Jenny stood nervously in front of the mirror, trying her hardest to remain calm and compose her nerves. With all the other girls out of the dressing room, she was alone to have her last minute breakdown. She held onto the dressing table as she breathed in and out, just as her mother had taught her after her first encounter with stage-fright back in elementary school.

"Jenny?" Eric's voice rang out from outside the room. "Is everything okay?"

"Yeah - Yeah. I'm fine. Just a little nervous," she said.

The dressing room door opened and Eric came barrelling in. With one look at his step-sister, he immediately knew what was going through her mind. He grabbed her hand and helped her settle into one of the armchairs.

"Hey, Jenny, what's wrong?" he asked softly.

"I - I'm scared," she admitted truthfully. "Remember what Blair said yesterday? That after today, there's no going back. Only forward. And I just feel like I'm leaving a part of myself behind. It's like saying goodbye to Jenny from Brooklyn and hello to a society that I don't even feel welcome in."

Knotting his hands in hers, Eric gave it a squeeze and said, "Jenny, you know that's not true. Just because you're integrating yourself into high society _doesn't_ mean you'll forget yourself. Think about all that happened last year - sure you went off the rails for a while, but you found yourself in the end, right."

He noticed the unshed tears in her eyes and continued, "Besides, not everyone is like Blair. Sure there are many classist snobs out there. But not everyone will look down on you just because of where you come from. In fact, some people may even root for you more because of it. Take the girls at Constance, for instance. They may not have liked or wanted you as queen at first, but eventually you won their respect, regardless of your background or status. If you can win them over, you can win anyone over."

With a deep, shaky breath, Jenny threw her arms around her step-brother and buried her face in his chest. "Thank you, Eric," she said, her voice muffled. "You always know what to say to make me feel better."

Eric chuckled. "It's a gift. Now come on, there's a crowd out there waiting for their queen to arrive."

* * *

"Hey, have you seen Graham anywhere?" Jenny asked her minions, who all shook their heads instantly. "Great. I'll just have to go find him before they start calling out our names. I'll see you all later."

With that, she made her way around the building, searching each room and coming up empty. At one point she bumped into Nate, who steadied her after she had almost lost her balance. He looked dapper in his black suit and bow tie and Jenny tried her hardest not to let that affect her.

"Hey, Jenny. You look nice. Have you seen Blair?"

"No. Not yet, fortunately. I'm looking for my escort, Graham Collins. He's, uh, sort of this year's, I guess, you."

The dimples on Nate's face stood out as he grinned in amusement. "I'll take that as a compliment," he said in good nature. "But, hey, have fun tonight."

"Thanks," Jenny said, tilting her head as she smiled at him. "I plan to."

After a while of searching, Jenny had almost given up when the organiser of the cotillion had asked all the participants to join them at the stage. Instead of following her fellow contestants, however, she continued prowling about the ballroom. Graham _had_ to be in there somewhere. She certainly wasn't going to the stage without an escort and embarrass herself in front of the entire Upper East Side. If she wanted to continue her reign as queen and break the social hierarchy at Constance, she had to get through the night and defy Blair's expectations.

Finally, she spotted Graham's shaggy brown hair sticking out of a darkened corner. She quickened her pace, intending to drag him out of there until she spotted who he was with. Particularly, whose mouth he had his tongue shoved down. _Jonathan's_.

For a second, she almost didn't believe what she was seeing. How could Jonathan, one of her best friends and boyfriend to her step-brother be playing tonsil hockey with Graham Collins? She squeezed her eyes shut and upon opening it again, found that Jonathan really was making out with Graham. Her eyes worked perfectly fine.

Eventually, the confusion faded and rage took its place. She was going to expose the duo, not only to Eric, but to the entire ballroom. She took a leaf out of Blair's handbook and made her way toward the lighting crew, with a request that was about to shake the entire evening.

* * *

"Miss Kira Abernathy, escorted by Mr. Eric Van Der Woodsen." Kira walked over to Eric, who clutched her arms and led her down the steps. Next, was Jenny's turn, which she was anxious to get over with.

"Miss Jennifer Tallulah Humphrey, escorted by Mr. Graham Collins," said the announcer. As anticipated, Graham was predictably absent from the stage, and Jenny had yet to move an inch from her position.

She noticed the confused looks on people's face, particularly from her father and Lily, but their questions were answered by a single spotlight beam which focused onto the hidden corner where Graham and Jonathan were making out. The crowd gasped at the sight, and the boys quickly jumped apart when they realised what had happened. Though she was delighted that her plan had worked, Jenny still felt a shred of remorse for doing that to Jonathan. But then again, he had just cheated on her best friend, and hell hath no fury like a woman scorned.

Squinting her eyes, she searched for Eric and found him close to tears, the very same way he had found her earlier on in the dressing room. She hurried forward, needing to catch up with him. She needed to comfort him and make him feel better about the entire ordeal. It wasn't his fault he was the victim.

"Eric!" she exclaimed, running after him in her heels. It was harder than it looked. "Eric! Please slow down."

Eventually he came to a halt and she took the opportunity to run up to him. "Eric, I'm so sorry about what happened."

This time the tears had let loose, and dripped down his face like an overflowing fountain.

"Did you know, Jenny?"

"No - not until tonight," she placed a comforting hand around his waist and pulled him closer, until he was fully engulfed in her arms. He sobbed on her dress and she let him, uncaring that it would get wet. "I was just as surprised as you are."

Just as she said that, he froze. "Wait, did you know about it before this all happened?"

"Uh, yeah. I was the one who orchestrated the spotlight."

Eric tore away from her arms as if she had just burnt him. She tried not to look hurt as he took several steps back. "Why on earth would you do that?"

She sighed, running her hand through her hair. "I don't know. I guess I was just angry at him for doing that to you, and my inner mean girl came out."

"No, don't try and use me as an excuse to justify your behaviour," he said, his voice no longer shaky and growing stronger with each word. He lifted a hand and wiped away all trace of tears, though his eyes remained red and puffy. "We both know why you did it. You didn't want Graham Collins embarrassing you like that. He was _your_ escort. You couldn't afford any slip ups that could cost you your crown."

"No, Eric. Please, it's not like that," she started, but he was having none of it. He threw her the dirtiest look he could muster and stormed away with nary a backward glance. Jenny stood frozen on the spot, feeling utterly helpless. She may have just lost her best friend.

* * *

 _Jenny Humphrey went to a ball. Jenny Humphrey had a great fall. And none of her minions, mentors or friends want to put Jenny together again. XOXO - Gossip Girl_

As she read the latest gossip girl blast, Jenny decided that she had finally had enough. She would walk down the steps with the hottest escort, prove herself to the entire Upper East Side and Blair, and get her best friend back. Eric was right about what he said earlier - she wasn't going to lose herself. Instead, she'd get back up and try again. It was time to fix everything.

Phone in hand, she dialled the one person she considered her knight in shining armour.

"Hi. Are you still here?"

* * *

"May I have your attention please?" the announcer addressed the audience into the microphone. "Due to extenuating circumstances, we still have one last debutante to present. Miss Jennifer Tallulah Humphrey, escorted by Mr. Nathaniel Archibald."

The crowd gasped in astonishment. The faces of Jenny's fellow peers ranged from utter bewilderment to downright awe. Jenny tried not to smirk as she walked over to Nate. He offered her his arm and she grabbed it gratefully. The two posed for pictures with smiles and for once, she felt the approving gazes from the other queens.

Even Blair congratulated her, a genuine smile on her face as she did so. With this surge of a power move, she had finally won their respects. She had won the crown. It was over.

So why did she feel so empty?

.

* * *

 _Ooo drama! I quite liked Blair in this chapter. Any thoughts?_


End file.
